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J Org Chem. 2015 Feb 6;80(3):1915-9. doi: 10.1021/jo5025333. Epub 2015 Jan 12.

A convergent approach to the total synthesis of telmisartan via a Suzuki cross-coupling reaction between two functionalized benzimidazoles.

Author information

1
Department of Chemistry and Department of Chemical and Life Science Engineering, Virginia Commonwealth University , Richmond, Virginia 23284, United States.

Abstract

A direct and efficient total synthesis has been developed for telmisartan, a widely prescribed treatment for hypertension. This approach brings together two functionalized benzimidazoles using a high-yielding Suzuki reaction that can be catalyzed by either a homogeneous palladium source or graphene-supported palladium nanoparticles. The ability to perform the cross-coupling reaction was facilitated by the regio-controlled preparation of the 2-bromo-1-methylbenzimidazole precursor. This convergent approach provides telmisartan in an overall yield of 72% while circumventing many issues associated with previously reported processes.

PMID:
25522005
DOI:
10.1021/jo5025333
[Indexed for MEDLINE]

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